Diisopropylethylamine → N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-4-methyl-2-(methyloxy)benzamide

HRID 42246

Reaktionsgleichung

Reaktionsgleichung von HRID 42246
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:11][CH3:12])[CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH:46]1[C:54]2[C:49](=[C:50]([C:55]3[CH:56]=[C:57]([NH2:64])[C:58]4[CH:59]=[N:60][NH:61][C:62]=4[CH:63]=3)[CH:51]=[CH:52][CH:53]=2)[CH:48]=[CH:47]1>CN(C=O)C>[NH:46]1[C:54]2[C:49](=[C:50]([C:55]3[CH:63]=[C:62]4[C:58]([CH:59]=[N:60][NH:61]4)=[C:57]([NH:64][C:6](=[O:8])[C:5]4[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][C:4]=4[O:11][CH3:12])[CH:56]=3)[CH:51]=[CH:52][CH:53]=2)[CH:48]=[CH:47]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 5971642-Methoxy-4-methylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 582680196-(1H-indol-4-yl)-1H-indazol-4-amine

Produkt 1

HCID 44540223N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-4-methyl-2-(methyloxy)benzamideAusbeute 16,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-methyl-2-(methyloxy)benzoic acid (67 mg, 0.40 mmol) in DMF (1 ml) were added HATU (248 mg, 0.40 mmol) and DIPEA (0.211 mL, 1.21 mmol). The mixture was stirred for 30 mins under nitrogen before addition of 6-(1H-indol-4-yl)-1H-indazol-4-amine (50 mg, 0.201 mmol). The reaction was stirred for 2 h then it was loaded onto PS-aminopropyl cartridge (5 g) and left for 3 h. The cartridge was washed with 10% MeOH in DCM. Appropriate fractions were combined and the solvent was evaporated. The residue was dissolved in MeOH: DMSO (1 ml; 1:1, v/v) and purified by Mass Directed Automated Preparative HPLC using method B. Solvent was evaporated under a stream of nitrogen to give title compound (13 mg).

Aufarbeitung

  1. waitleft for 3 h
  2. washThe cartridge was washed with 10% MeOH in DCM
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in MeOH
  5. custom1:1, v/v) and purified by Mass Directed Automated Preparative HPLC
  6. customSolvent was evaporated under a stream of nitrogen

Quellen und Nachweise

ORD-Eintrag
ord-f3a738058af44b96a6d517d617084b40
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536169B2

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